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Top 10 Best Hawaii Sailing Trips

Found 114 Sailing Trips activities in Hawaii. Sort by Popularity. - Page 2
 

'Alihilani Lahaina Sunset Sail

(4.9 of 109 reviews)

We pride ourselves on sailing, so enjoy the natural sounds as we turn of our motors and raise our sails. Our spacious catamarans make for a luxurious experience, allowing for incredible views of Maui and the inter islands from the... More

Free Cancellation
Start From $117.30
 
'Alihilani Lahaina Sunset Sail

'Alihilani Lahaina Sunset Sail

  • Hawaii
  • Superb109 reviews4.9

We pride ourselves on sailing, so enjoy the natural sounds as we turn of our motors and raise our sa....

    Free Cancellation
    Start From $117.30
 
 

Honolulu Sunset Sail from Kewalo Harbor Including Drinks

(4.8 of 186 reviews)

Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 21+ with valid ID to consume alcoholic beverages). Sail the south shore from Kaka'ako Waterfront to Waikiki, with beautiful views ... More

Free Cancellation
Start From $61.50
 
Honolulu Sunset Sail from Kewalo Harbor Including Drinks

Honolulu Sunset Sail from Kewalo Harbor Including Drinks

  • Hawaii
  • Superb186 reviews4.8

Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 2....

    Free Cancellation
    Start From $61.50
 
 

Waikoloa Signature Catamaran Sunset Sail

(4.7 of 405 reviews)

End your day in paradise with a relaxing sunset cruise along Waikoloa’s beautiful Kohala Coast. Departing from Anaeho‘omalu Bay, the Spirit of Aloha catamaran offers a smooth, comfortable ride with panoramic views of Mauna Kea... More

Free Cancellation
Start From $159.00
 
Waikoloa Signature Catamaran Sunset Sail

Waikoloa Signature Catamaran Sunset Sail

  • Hawaii
  • Superb405 reviews4.7

End your day in paradise with a relaxing sunset cruise along Waikoloa’s beautiful Kohala Coast. De....

    Free Cancellation
    Start From $159.00
 
 

Waikiki Sunset Cruise from Oahu

(4.8 of 60 reviews)

Experience a Hawaiian sunset sail aboard our 55-foot double-decker catamaran. With spacious decks and a submerged glass-bottom viewing room, you’ll have an ideal vantage point to observe marine life such as dolphins, whales, sea... More

Free Cancellation
Start From $45.00
 
Waikiki Sunset Cruise from Oahu

Waikiki Sunset Cruise from Oahu

  • Hawaii
  • Superb60 reviews4.8

Experience a Hawaiian sunset sail aboard our 55-foot double-decker catamaran. With spacious decks an....

    Free Cancellation
    Start From $45.00
 
 

Waikiki Sunset Cocktail Cruise - Hilton Hawaiian Village

(4.6 of 25 reviews)

Explore the Waikiki coastline aboard the new Spirit of Aloha, a 65-foot sailing catamaran custom-built for the Hilton Hawaiian Village Waikiki Beach Resort. See the island like never before as you set sail from the only pier in W... More

Free Cancellation
Start From $119.95
 
Waikiki Sunset Cocktail Cruise - Hilton Hawaiian Village

Waikiki Sunset Cocktail Cruise - Hilton Hawaiian Village

  • Hawaii
  • Superb25 reviews4.6

Explore the Waikiki coastline aboard the new Spirit of Aloha, a 65-foot sailing catamaran custom-bui....

    Free Cancellation
    Start From $119.95
 
 

Half-Day Deluxe Molokini Snorkel Excursion in Maui

(4.9 of 116 reviews)

Begin your morning with a chef-prepared buffet breakfast as we cruise to Molokini Crater, a world-renowned marine preserve home to over 400 species of tropical fish and coral reefs. Your adventure continues with a second snorkel... More

Free Cancellation
Start From $309.00
 
Half-Day Deluxe Molokini Snorkel Excursion in Maui

Half-Day Deluxe Molokini Snorkel Excursion in Maui

  • Hawaii
  • Superb116 reviews4.9

Begin your morning with a chef-prepared buffet breakfast as we cruise to Molokini Crater, a world-re....

    Free Cancellation
    Start From $309.00
 
 

Afternoon Sail & Snorkel to the Captain Cook Monument

(4.9 of 733 reviews)

A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient lava flows. As you arrive at the "World Famous Captain Cook Monument" your snorkeling a... More

Free Cancellation
Start From $136.19
 
Afternoon Sail & Snorkel to the Captain Cook Monument

Afternoon Sail & Snorkel to the Captain Cook Monument

  • Hawaii
  • Superb733 reviews4.9

A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathta....

    Free Cancellation
    Start From $136.19
 
 

Snorkel with Manta Rays Guaranteed

(4.8 of 750 reviews)

Join us aboard our luxurious catamaran, Hoku Nui, as we coast to the world famous Manta Ray Village. Travel Channel says “its one of the top ten things to do in your life time”, and Sea Paradise has been offering its guests th... More

Free Cancellation
Start From $141.57
 
Snorkel with Manta Rays Guaranteed

Snorkel with Manta Rays Guaranteed

  • Hawaii
  • Superb750 reviews4.8

Join us aboard our luxurious catamaran, Hoku Nui, as we coast to the world famous Manta Ray Village.....

    Free Cancellation
    Start From $141.57
 
 

Snorkel Sail Adventure off Ka'anapali Beach, Maui

(4.9 of 39 reviews)

While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You will see a variety of tropical fish, and if you’re lucky, an endangered Hawaiian Green Sea turtle called a ‘Honu’. A hot buff... More

Free Cancellation
Start From $192.17
 
Snorkel Sail Adventure off Ka'anapali Beach, Maui Likely to Sell Out

Snorkel Sail Adventure off Ka'anapali Beach, Maui

  • Hawaii
  • Superb39 reviews4.9

While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You w....

    Free Cancellation
    Start From $192.17
 
 

Maui Sunset Sail

(4.6 of 218 reviews)

Enjoy tantalizing pupus (appetizers) and island-style music against the backdrop of a stunning sunset over the Pacific Ocean.This relaxing cruise is aboard our luxury sailing catamaran, Ocean Spirit. It’s the perfect way to expe... More

Free Cancellation
Start From $137.82
 
Maui Sunset Sail Likely to Sell Out

Maui Sunset Sail

  • Hawaii
  • Superb218 reviews4.6

Enjoy tantalizing pupus (appetizers) and island-style music against the backdrop of a stunning sunse....

    Free Cancellation
    Start From $137.82
 
 

Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea

(4.8 of 298 reviews)

Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos with the rainbow sails and also the beautiful scenery with Diamond head in the background. The net is also a fun ride and you’ll g... More

Free Cancellation
Start From $72.96
 
Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea Likely to Sell Out

Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea

  • Hawaii
  • Superb298 reviews4.8

Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos wi....

    Free Cancellation
    Start From $72.96
 
 

Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)

(4.7 of 53 reviews)

Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui sunset begin to paint the sky. As you step aboard, you're greeted by the friendly crew who welcome you with warm aloha spirit. The c... More

Free Cancellation
Start From $289.00
 
Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only) Likely to Sell Out

Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)

  • Hawaii
  • Superb53 reviews4.7

Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui su....

    Free Cancellation
    Start From $289.00
 
 

Waikiki: 2-Hour Whale Watching with Guaranteed Sightings on Oahu

(4.6 of 1,334 reviews)

Humpback whales visit Hawaii each year and give birth in our warm tropical waters, it's a once in a lifetime experience that you will never forget to see this amazing creature. If you are lucky enough, you might see dolphins, sea ... More

Free Cancellation
Start From $53.31
 
Waikiki: 2-Hour Whale Watching with Guaranteed Sightings on Oahu Likely to Sell Out

Waikiki: 2-Hour Whale Watching with Guaranteed Sightings on Oahu

  • Hawaii
  • Superb1,334 reviews4.6

Humpback whales visit Hawaii each year and give birth in our warm tropical waters, it's a once in a ....

    Free Cancellation
    Start From $53.31
 
 

Hilton Hawaiian Village Turtle Snorkel with Optional Lunch

(4.6 of 40 reviews)

Swim with turtles and fish, while enjoying the crystal blue topical waters. Sail the scenic Waikiki coastline and snorkel at Turtle Canyon. Our eco-conscious cruise lets you see whales (December through March), fish, even green s... More

Free Cancellation
Start From $109.95
 
Hilton Hawaiian Village Turtle Snorkel with Optional Lunch Likely to Sell Out

Hilton Hawaiian Village Turtle Snorkel with Optional Lunch

  • Hawaii
  • Superb40 reviews4.6

Swim with turtles and fish, while enjoying the crystal blue topical waters. Sail the scenic Waikiki....

    Free Cancellation
    Start From $109.95
 
 

Waikiki: Fireworks Cruise from Beach & Cocktail Open Bar | Oahu

(4.8 of 58 reviews)

Set sail with Waikiki’s top-rated fireworks cruise and enjoy the famous Hilton Hawaiian Village display from the best seat on Oahu—the water. Every Friday night, you’ll glide along the coastline and experience an exclusive o... More

Free Cancellation
Start From $90.01
 
Waikiki: Fireworks Cruise from Beach & Cocktail Open Bar | Oahu Likely to Sell Out

Waikiki: Fireworks Cruise from Beach & Cocktail Open Bar | Oahu

  • Hawaii
  • Superb58 reviews4.8

Set sail with Waikiki’s top-rated fireworks cruise and enjoy the famous Hilton Hawaiian Village di....

    Free Cancellation
    Start From $90.01
 
 

Deluxe Sail & Snorkel to the Captain Cook Monument

(4.9 of 478 reviews)

Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient lava flows. As you arrive at the "World Famous Captain Cook Monument" your snorkeling adventure will begin in the turquoise waters... More

Free Cancellation
Start From $179.27
 
Deluxe Sail & Snorkel to the Captain Cook Monument Likely to Sell Out

Deluxe Sail & Snorkel to the Captain Cook Monument

  • Hawaii
  • Superb478 reviews4.9

Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient ....

    Free Cancellation
    Start From $179.27
 
 

Paragon Lahaina Sunset Sail

(4.3 of 6 reviews)

Join us aboard our flagship sailing catamaran, Paragon, for an unforgettable Maui sunset sail from Lahaina Harbor. Enjoy the afternoon hours at sea in the glassy, miraculous ‘au’au Channel is like floating inside an infinite ... More

Free Cancellation
Start From $102.00
 
Paragon Lahaina Sunset Sail Likely to Sell Out

Paragon Lahaina Sunset Sail

  • Hawaii
  • Exellent6 reviews4.3

Join us aboard our flagship sailing catamaran, Paragon, for an unforgettable Maui sunset sail from L....

    Free Cancellation
    Start From $102.00
 
 

2-Hour Oahu Sunset Catamaran Sail

(4.8 of 129 reviews)

Relax, sit back and delight in our 2-hour sunset sailing cruise on a gorgeous, 53' foot catamaran from the beautiful Ko Olina Marina on Oahu. Sip a cocktail and enjoy warm wind in your hair as you scan for dolphins and listen for ... More

Free Cancellation
Start From $130.00
 
2-Hour Oahu Sunset Catamaran Sail Likely to Sell Out

2-Hour Oahu Sunset Catamaran Sail

  • Hawaii
  • Superb129 reviews4.8

Relax, sit back and delight in our 2-hour sunset sailing cruise on a gorgeous, 53' foot catamaran fr....

    Free Cancellation
    Start From $130.00
 
 

Waikoloa Catamaran Snorkel Sail Including Lunch

(4.6 of 109 reviews)

Set sail from Anaeho‘omalu Bay on a 3-hour snorkel and cruise adventure along Waikoloa’s beautiful Kohala Coast. Aboard the spacious Spirit of Aloha catamaran, enjoy a smooth, comfortable ride to one of the region’s best sno... More

Free Cancellation
Start From $189.00
 
Waikoloa Catamaran Snorkel Sail Including Lunch Likely to Sell Out

Waikoloa Catamaran Snorkel Sail Including Lunch

  • Hawaii
  • Superb109 reviews4.6

Set sail from Anaeho‘omalu Bay on a 3-hour snorkel and cruise adventure along Waikoloa’s beautif....

    Free Cancellation
    Start From $189.00
 
 

Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure

(4.7 of 959 reviews)

Snorkel Turtle Canyon on the Largest Luxury Catamaran! Top Quality Gear, Certified Crew & Premium On Board Bar. When you trust Moana Sailing Co. for your snorkel adventure, you’re choosing the tour with the most professionalis... More

Free Cancellation
Start From $84.99
 
Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure Likely to Sell Out

Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventu....

  • Hawaii
  • Superb959 reviews4.7

Snorkel Turtle Canyon on the Largest Luxury Catamaran! Top Quality Gear, Certified Crew & Premium On....

    Free Cancellation
    Start From $84.99
 
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